Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

Dominik Koszelewski*, Anna Brodzka, Arleta Madej, Damian Trzepizur and Ryszard Ostaszewski*

*Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warszawa, Poland, Email: dominik.koszelewskiicho.edu.pl, ryszard.ostaszewskiicho.edu.pl

D. Koszelewski, A. Brodzka, A. Madej, D. Trzepizur, R. Ostaszewski, J. Org. Chem., 2021, 86, 6331-6342.

DOI: 10.1021/acs.joc.1c00154

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Abstract

Benzylidene 1,1-diacetate is a sustainable and efficient acyl donor for enzymatic acylation of chiral and nonchiral alcohols. Especially, unsaturated acetates can be converted without E/Z isomerization. The acyl donor can be recreated and reused. A dynamic kinetic resolution (DKR) protocol results in chiral acetates in high yields and very high enantiomeric excesses.

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Key Words

Acetates, Acylation, Asymmetric Acylations of Alcohols

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ID: J42-Y2021